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At the end of parashas Toldos (28:6-8), the pesukim indicate factors in Esav's decision to add Machalas, who was not a Canaanite, as a spouse:

א וַיִּקְרָא יִצְחָק אֶל-יַעֲקֹב, וַיְבָרֶךְ אֹתוֹ; וַיְצַוֵּהוּ וַיֹּאמֶר לוֹ, לֹא-תִקַּח אִשָּׁה מִבְּנוֹת כְּנָעַן. ב קוּם לֵךְ פַּדֶּנָה אֲרָם, בֵּיתָה בְתוּאֵל אֲבִי אִמֶּךָ; וְקַח-לְךָ מִשָּׁם אִשָּׁה, מִבְּנוֹת לָבָן אֲחִי אִמֶּךָ. ג וְאֵל שַׁדַּי יְבָרֵךְ אֹתְךָ, וְיַפְרְךָ וְיַרְבֶּךָ; וְהָיִיתָ, לִקְהַל עַמִּים. ד וְיִתֶּן-לְךָ אֶת-בִּרְכַּת אַבְרָהָם, לְךָ וּלְזַרְעֲךָ אִתָּךְ--לְרִשְׁתְּךָ אֶת-אֶרֶץ מְגֻרֶיךָ, אֲשֶׁר-נָתַן אֱלֹהִים לְאַבְרָהָם. ה וַיִּשְׁלַח יִצְחָק אֶת-יַעֲקֹב, וַיֵּלֶךְ פַּדֶּנָה אֲרָם--אֶל-לָבָן בֶּן-בְּתוּאֵל, הָאֲרַמִּי, אֲחִי רִבְקָה, אֵם יַעֲקֹב וְעֵשָׂו. ו וַיַּרְא עֵשָׂו, כִּי-בֵרַךְ יִצְחָק אֶת-יַעֲקֹב, וְשִׁלַּח אֹתוֹ פַּדֶּנָה אֲרָם, לָקַחַת-לוֹ מִשָּׁם אִשָּׁה: בְּבָרְכוֹ אֹתוֹ--וַיְצַו עָלָיו לֵאמֹר, לֹא-תִקַּח אִשָּׁה מִבְּנוֹת כְּנָעַן. ז וַיִּשְׁמַע יַעֲקֹב, אֶל-אָבִיו וְאֶל-אִמּוֹ; וַיֵּלֶךְ, פַּדֶּנָה אֲרָם. ח וַיַּרְא עֵשָׂו, כִּי רָעוֹת בְּנוֹת כְּנָעַן, בְּעֵינֵי, יִצְחָק אָבִיו. ט וַיֵּלֶךְ עֵשָׂו, אֶל-יִשְׁמָעֵאל; וַיִּקַּח אֶת-מָחֲלַת בַּת-יִשְׁמָעֵאל בֶּן-אַבְרָהָם אֲחוֹת נְבָיוֹת, עַל-נָשָׁיו--לוֹ לְאִשָּׁה.

The following factors are implied:

Esav saw that-

  1. Yitzchak blessed Yaakov
  2. Yitzchak sent Yaakov away from Canaan to find a wife
  3. Yitzchak told Yaakov not to marry a Canaanite
  4. Yaakov listened to his parents and left

The result being that Esav saw that his father was against marrying Canaanites.

-#3 is certainly a factor in the decision. #2 is related, but seemingly extraneous. #1 and #4 don't seem to be connected. This has bothered me for a while. Any ideas?

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2 Answers

Daas Sofrim explains them as follows:

#1 and #2: "Yitzchak blessed Yaakov... and commanded him not to marry a Canaanite wife": these form a continuum - Yaakov is not to marry a Canaanite (a member of an accursed nation) because he had received the blessing. This told Eisav, then, that the blessings that Yaakov had "stolen" weren't just a fluke; Yitzchak is concerned that these should have a future too. (Put differently, then: had Eisav received the blessings, he'd be the one now barred from marrying Canaanites.)

#3: "Yaakov listened... and went to Padan Aram": Eisav has now learned a new lesson about the extent to which one must honor his parents (he who excelled in this mitzvah, as Chazal tell us). Yaakov has not only left home despite the difficulty involved, but he is prepared to forgo his independence in choosing a mate and to leave the decision up to his parents - by contrast with Eisav, who had taken his own initiative in deciding whom to marry.

#4: therefore, "Eisav now saw" how important a proper match is in his parents' eyes, and indeed realized for the first time that Yitzchak is perturbed by the behavior of the women he has married.

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(Our #'s don't line up. My comment will use the #'s delineated in the question.) So, a skeletal summary would be: 1, 2 and 3 deal with the importance of marrying out of Canaan and its effect on lineage. #4 gave Esav the wherewithal to follow through. –  YDK Nov 23 '11 at 15:45
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From the new Kehot Chumash's Interpolated Translation (bold is direct translation of the verse, regular is the explanation culled from various sources, most of them from the Lubavitcher Rebbe's Sichot, see link for sources). I have added the numbers to mark the parts I think correspond to your question:

9 So Esau went off immediately, trying to flaunt his alacrity, to his uncle Ishmael, and married his cousin Machalat, daughter of Abraham's son Ishmael, (4) in order to show that he was no less deferential to his father's wishes than was his brother, Jacob; in fact, he was even more deferential to his father's wishes, because Jacob had been explicitly instructed to marry a family girl whereas he did so of his own volition. For two reasons, however, Esau did not follow Jacob to Padan Aram to marry one of his cousins from the royal line of Shem: (1)(2) Firstly, he understood that Jacob had gone there in order to fulfill Isaac's blessings, and he knew very well that he was no longer party to these blessings. (3) And secondly, he sought to outdo Jacob—who went to marry a girl who was merely a member of Abraham's extended family—by marrying a girl who was Abraham's direct descendant.

So to sum it up, Eisav saw that Yitzchok blessed Yaakov and sent him to Padan Aram to marry and fulfill those blessings, and Yaakov listened right away. He decided to show Yitzchok that he could do better than Yaakov, so, without even being asked, he right away married Machlat, Avraham's granddaughter, as opposed to someone who was only a descendant of Avraham's brother. He didn't leave Canaan to find a wife, since Yaakov went to fulfill the brachot Yitzchok gave him (I believe this refers to the blessing directly connected to going to Padan Aram (Bereshit 23:1-4), not the blessings that Yaakov took from Eisav), which Eisav did not receive.

I think this addresses everything Eisav saw.

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